How Improv and Business (and Everything) are Related

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Maybe it’s the changing of the seasons bringing it out in people, but I feel like I’ve seen a big change in everyone’s attitudes around me. It isn’t like night or day; it’s more like they’ve become more intense versions of themselves. If they were discouraged about their plans, they’re more desperate now. If they were slightly enthused, they are full-blown optimistic now.

That is, to use a first-grader’s vocabulary, good.

What isn’t is that I feel like many entrepreneurs I run into or know or work with are becoming cockier. Like becoming a stand-up comedian or any sort of performer, you need to have a few things off about you to give you the audacity to think you can strike your own path, not work a traditional job-job and shift the world to your will to support yourself with your own ideas. Nobody came into this world hoping to punch a clock -- whatever that means -- but what I’ve noticed is there’s a lot of people who have a nose-in-the-air attitude about it without anything to really back it up.

Call it paying dues or keeping an open mind, but in improv, it’s called “yes, and”-ing. This isn’t a plug for my other gigs, but I started teaching at Second City recently and it’s reintroduced my mind to the fundamentals of improv. Second City has a business outreach department called BizCo, which applies its sketch-writing techniques to communicating internal issues at businesses.

It’s easy to mock, but I think people forget that some of the most basic playground rules apply when dealing with each other and flexing your almighty hustle muscles. When I speak about “yes, and”-ing, it means I say something to you. You could say no, but that would end everything immediately because we are having a conflict and you are disagreeing. If you say “yes, and…” and add to what I’ve said, we both get something out of it.

I’m not naming names, nor do I even have anyone specific in mind. But I think entrepreneurs should keep in mind what others can do for them and why it behooves them to listen and add to the conversation -- not just wait for their chance to talk about themselves.

It’s a season of change. So. For a change of pace, why not see what others have to offer and, all cheesiness aside, help make the world a much better place together?

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.